First week of college and how I [f]ailed to lose my virginity in the weirdest of ways

So I’ve been waiting for this moment for a long time. By “this moment”, I mean the moment I’d get to recall the night I lost my virginity, write it down, and share the experience with everyone here. I’ve read so many stories to satisfy myself in the past I felt like I needed to give back.

Well, that was the plan, anyway. You might think that’s weird, and it probably is. I’m 19, a girl, and I just started my freshman year of college. I also have a bad addiction to reading these kinds of naughty stories. My parents were really, really strict with me in terms of boys in middle/high school. I’ve had a couple boyfriends here and there, but they never let me out of their sight with him around and needless to say I ended up coming to college a virgin.

Of course, they were strict but not really smart about it. I kinda figured out how to touch myself early on, and although they kinda tightened up on what I use the computer for when they caught me masturbating one day, they couldn’t keep me from reading. So I satisfied all my urges reading, pretty much. A fun thing to do was for me to just use the family computer and read a raunchy story while my parents were around, pretending to be working on an essay when really the “essay” was a word doc of something I copy-pasted from here.

Anyway, I had one goal when I got to college. Well, two, I guess. One was to graduate. The other was to lose my virginity, ASAP. I just needed to know what it felt like. I wasn’t going to be some tramp that ran around hopping from one dick to another, but I knew I would go crazy if I didn’t just let myself have that one. …maybe I already was crazy. I don’t know.

I didn’t know if the stories and stuff I had heard about crazy frat party orgies and whatnot were true or not. I suspected that it wasn’t, and it was more tame, but I had to find out. I didn’t want to obviously jump in with an orgy, but hey, I figured what frat guy wouldn’t want the chance to take a girl’s virginity, right?

I found out that the beautiful part of the beginning of the semester is that there are parties virtually every night of the week so that people can show off their organizations and how fun they are. It was perfect. My roommate and I got invited to a party from a guy that walked us home from a (much less sexual, actually kinda cool) club meeting, and I thought “Oh my god. This is it.”

Last night, the night of the party, my roommate backed out on going so I called the guy to walk me there to keep me company and introduce me to a few people. He quickly came to pick me up and told me I looked great. I was wearing a short, red dress that just gave enough of my thighs away with a white bra, a lacy “push-up” that really doesn’t do THAT great of a job considering I’m only a 30A. Still, it was the best one I had to show a little chest. And I wore a matching white thong. I just wore sandals since I hate being too tall – I’m 5’11 naturally so I try to avoid towering over guys. If this helps, I’m a brunette with pretty long, curly hair.

All the while he’s walking me to the party, my heart keeps thumping because I’m so nervous. I’m suddenly more apprehensive than I was before. I tried to imagine him penetrating me. It was okay, though he wasn’t 100% my type. I realized I DID have a few hiccups about who I wanted my first one to be. It was also hard to bring up. I tried to bring it up like it was no big deal. I asked him “So, like, do people hook up a lot at your parties?” He said it depended whether you were into that or not. He told me to brace myself for the flurry of guys that would make those moves, but assured me no one would force me to do anything I didn’t want to do. Perfect, I thought.

The party was at their frat house and my first thought was “Jesus it is hot in here” and my second thought was “Oh my god it smells so weird.” On one hand it smelled great – there was some sort of cookout-thing in the backyard and that was good, but then the alcohol and sweat and people just made a weird funky smell. It was weird. I got lost in the flurry of everything really quickly. The guy that took me there introduced me to a few people and then he was lost in a sea of people and I kinda made my way through the house, aiming for nowhere in particular. A guy came up to me, and I think his name was Paul, and he offered to get me a drink. I say “I think” not for the story’s sake but because I genuinely can’t remember. We made some small talk while he made me a drink. It wasn’t my first brush with alcohol but I felt it almost immediately. The last thing I wanted to do was barf all over the place, so I took a few more sips, put it down, and went to the backyard to dance a bit. Guys came here and there to dance with me and we would chat, but no one really seemed “IT” to me. I felt so many boners on my ass, though, and it started to drive me a little nuts.

I went to the bathroom at some point and while I was waiting for it to open, I started talking to this guy, Leo. He was it. I knew it almost immediately. I loved his voice, his body, he was taller than I was, he was perfect. He was nice and built but not like disgustingly muscular. And he was so nice! And he was checking me out here and there, which was really reassuring. At this point he probably could’ve felt the moisture coming from my legs. He waited for me while I used the bathroom, and when I came out he offered to make me a drink. We chatted in the kitchen for a bit, and he put his arm around my waist. I jokingly told him if he kept getting me more drinks he would be stuck with walking me home. He said it wouldn’t be a problem because I could just crash upstairs in his room. My heart was pounding. I’m pretty sure I was a little tipsy, but I was in laser focus mode because this was how it was going to happen. I decided to just go for it. I asked him to show me his room because I needed to lay down. He smiled and led me upstairs to the third floor. On the way up he gently groped at my ass. I giggled and gave him a kiss on the staircase. We made out for a bit, and he immediately reached under my dress to grab a handful of my ass.

We stumbled into his room and we began kissing, groping each other. I shoved my hands into his pants and felt a real, live, warm cock for the first time in my life. I felt the blood just rush to everywhere in my body. I jerked it off inside his pants, and he furiously clawed at my chest. When his finger first hit my pussy over my thong, I let out a moan that sounded more like a yelp.

“Sorry,” he said. “Did I hit something?”

“No, no,” I panted. “It’s just..first time.”

His eyes opened up and I gave him a nod. I told him this is my first time doing anything like this with a guy. He said it was no problem.

He took off his pants, and I slid off my dress. I took off my bra as he got completely naked. He threw me on the bed and I opened my legs for him before a thought came into my head.

“Can I suck your cock?” I asked, purring. He immediately sat back on the bed and invited me forward. I leaned toward his cock, taking it in my hands, and put my mouth on it. It was weird, a warm, salty, but weirdly good tasting thing. I had the impulse to actually suck it, but he quickly tapped me and told me not to do that. I licked it for a little while, then I tried to do what I usually saw, just running my mouth and tongue over it as slowly and sensually as I could, sometimes stroking it, all in what I thought was good rhythm. He stopped me after a few seconds and just told me to relax and open my mouth.

I obeyed, and I just opened my mouth and relaxed. He took my hair, grabbed my head, and told me to just barely close my lips on his cock in my mouth. I did so. He began to slowly pump in and out of my mouth, and I finally got it. I let his hands control me, his cock fucking my mouth. He sped up a little faster, and I felt it hit the back of my throat a couple of times. It made me gag and I had to tell him to stop for a second.

He was in full on mode now, though. As soon as I took my mouth off of his cock, he turned me on my back and got some lube and a condom from his endtable’s drawer. He put on a condom. He lubed up his cock. I closed my eyes, waiting for it. I was so wet and ready.

And then I felt a finger in my ass. He was lubing up my ass.

“Wait, what?” I asked. I wasn’t objecting, more confused.

“I need your ass babe,” he said. I had no idea what to do or say. I was just floored. Before I could do or say anything, I felt him lift up my hips and I felt it, his cock, push against my asshole.

I had promised myself I wouldn’t cry at my first penetration, but I was not prepared for that being anal. I bit into his pillow as his cock pushed in a little by little into my ass. I was so fucking horny, I didn’t even protest. I couldn’t protest, really, because I was in so much pain. But through the pain, oh my god it felt good. I willed my asshole to stretch out and accept his cock.

But it just hurt too much. “No, Leo, wait, just hold on..” I managed to gasp that out loud before he suddenly grunted and I felt his cock pulse once, twice, three times, and an unmistakeable warmth was in my ass. He came. And I was suddenly somewhat disappointed.

He pulled out and threw the condom off onto the floor. I kinda just laid there, surprised, shocked, I don’t even know. He was panting, kept saying how amazing that was, how he had never fucked an ass before. Well, I wanted to say, I’ve never been fucked anywhere before and this was certainly an experience.

The night seemed over after that. I had my pleasure, but it wasn’t enough to make me cum. I put my clothes back in, Leo and I talked a bit more, but he clearly didn’t seem all that into me anymore. It kinda sucked, not because I was expecting some grandiose romance to come out of this but because I didn’t even lose my virginity AT ALL.

…so, here I am, writing this on a Friday evening. I’ve got no plans tonight but hopefully tomorrow night something will happen. And when that time does come, I hope I can share it with you all!

xox, Hal

Source: reddit.com/r/gonewildstories/comments/3jogwz/first_week_of_college_and_how_i_failed_to_lose_my