Diary of a Slut: Losing Virginity

You never forget your first time, no matter how good—or bad—it was. And even though mine was only a few months ago, and everything is still fresh in my mind, I don't think I'll ever not be able to remember every single detail. It was both an incredible experience and a horrible one at the same time, and a total accident.

I never planned on losing my virginity. Well, I knew I would at some point, just not then...not that night, and not the way it happened. I went to that party with zero intentions of doing anything like that. And that wasn't because I'd never been to a party before and didn't know what to expect; sure, sometimes things got crazy—especially at these parties—but I never went too far. At most I planned on having a few drinks, maybe get a little tipsy, and have some fun with my friends, and maybe even flirt with a few cute boys. But that was all. No way was I going to go any further than some kissing and harmless messing around.

Mostly everyone I knew had lost their virginity, but not me. I was the good girl, the one who waited. Of course I was never sure if I planned it that way or it just happened, but by the time spring semester came around there were only a few of us who hadn't done the deed yet.

And that was perfectly fine with me because, honestly, having sex had never been a big deal to me, one way or the other. I didn't care that I was a virgin, or that I hadn't gone very far with a boy yet—which, in itself, was odd because I had been boy-crazy for as long as I could remember. I might not have gone all the way yet (or any of the way, that is), but I was the little girl in kindergarten staring across the room at Patrick because he was so cute with his blue eyes and dimples, the one who never thought boys were "gross"—even though I played along with my friends and said they were. We called them names and ran away, but I was only pretending; secretly I sat up at night dreaming about them kissing me behind the tree in my backyard.

But maybe that's why not having sex was so easy for me. I'd been pretending to not want to do anything with a boy since I was seven and first learned what a "French Kiss" was that it had become commonplace. I was content to finish my last couple of months of high school, and probably even start college, pure. After making it all this way—to my eighteenth birthday and beyond—I certainly wasn't going to lose my virginity in some cliche way, like at prom in the back of a limo or something. Nope. Not happening.

Anyway, the whole virginity thing had never been a big issue for me, and then when Lauren, one of my two best friends, lost hers—to one of the hottest guys on the football team—it changed something inside of me. Now I was the only one in our trio (Becky, the first one to lose it, was the other) who hadn't had sex yet. But instead of becoming determined to lose it and join the club—which would have made way more sense—I started wearing my purity as a badge of honor. I was proud of it, and and planned to keep it.

And then Tommy Doyle's party happened. Tommy Doyle was the oddest of the odd; he was way too weird to be cool, and he didn't really have any close friends, but everyone loved him anyway. Part of it was his insanely cool and mega-hot older brother Johnny, and part of it was his parents were loaded. They lived in this huge house in the woods overlooking the lake, and once or twice a year Tommy and his brother would throw these amazing parties when their parents went out of town. I have no idea how they didn't find out, but Tommy and Johnny never seemed to get in trouble.

You'd get a special invite sneaked into your locker a couple of weeks before the party, and practically everybody in school went. Of course there were those who said the parties were lame and that they didn't want to go, but they always showed up anyway—claiming they only came to make fun of the rest of us. Right. Whatever. Who cares, really, because I never thought about not going. I always had a good time. Lots of fun, lots of cute boys, and something crazy would happen that'd be talked about for weeks afterwards.

I went with my usual crew...Lauren and Becky, and me. Lauren, like always, drove us in her mom's Range Rover. By the time we arrived the music was blaring, drinks were flowing, people were in the pool, and everyone was partying. I dressed sexy, but not overly slutty like some people. Becky—I'm looking at you! Her boobs were popping out of her shirt, and her skirt as so small and tight you could practically see everything. She looked like she was coming to this party just to get fucked. And maybe she was, but whatever. Good for her.

I dressed a little more conservatively...wearing a pair of denim shorts, a black crop top, and a cute pair of sandals. Of course I also put on my "sexy underwear", a black thong that was terribly uncomfortable, but I loved wearing. Even though I knew no one would see it or know, wearing it made me feel sexy and more confident. Glancing in the mirror before I left I thought I looked pretty good, hot even, but not I'm easy or I wanna fuck your brains out hot.

The first hour or so of the party went as expected. I had a few drinks, laughed with my friends, and talked and danced with a couple of cute boys. The only real excitement was when Johnny stripped naked and dove off his second floor balcony into the pool. (Unfortunately, I was inside playing Never Have I Ever—which is kind of humiliating when there's so much on your Never Have I Ever list—when that happened, and only heard about it afterwards.)

Anyway, by the time Ethan approached me I'd been at the party for a while, was feeling a little buzzed, and having a decent time. A group of us were sitting around the den...drinking, talking, and playing games. Some were even going a little further, getting frisky...not that it bothered me. It was fun.

I'd never met Ethan before; he was a friend of Johnny's from college, and ridiculously hot. There was something about him, too, that made it so easy to like him. He plopped himself down on the couch, squeezing in next to me and just started blabbing away...talking about anything and everything. He was charming and complimentary, telling me how pretty I was, how hot my outfit looked, and how much fun it was getting to know me. It was so easy getting lost in his captivatingly deep voice, sensual green eyes, and adorable dimples. And it didn't hurt that he was sitting so close I could literally feel his muscles flex when he moved.

Before I knew it he was rubbing my shoulders—but not in that creepy I'm-making-a-move-on-you kind of way—and whispering things in my ear that made me giggle and blush. Even though there were people all around us, Ethan made me feel like I was the only person in the world.

When he first leaned in to kiss me I was feeling shy and nervous, but half the people in the room were already crawling all over each other. I closed my eyes, leaned toward him and met his lips. I opened my mouth and felt the tips of our tongues connect, and it was heaven, better than any kiss I'd gotten before. He tasted sweet and salty, yummy and warm, and was very talented with his lips. Quickly I'd forgotten about everything else, wrapped my arms around his neck and fell backwards into the couch cushions.

Ethan was so good at this...he kissed me, nibbled on my neck and ears, and knew what he was doing. His touch was electric, touching me just enough, in the right way and in the right spots to keep me from stopping him...and desperately wanting more. His hands were caressing their way up and down my thighs and hips, working their way around to my butt, and then up the sides of my abdomen. His fingers slipped under the sides of my shirt, and I jumped when one of them brushed up against the side of my breast. (No boy—no one but me—had ever touched me there before.)

It was all moving so fast, faster I ever had, but it was fun and I felt powerless to stop it—not that I wanted to stop it. I couldn't believe how far I was letting him go...and how much I was enjoying it, and wanted him to do more. His hands, big and strong, were massaging my breasts (over my shirt), rubbing and squeezing them, and it felt amazing.

"You have the tiniest little nipples," Ethan said, flicking at them through my shirt. "They're so cute." I hadn't even realized they were—barely—poking out. And then in one quick motion he slipped both his hands completely inside my shirt and started caressing and massaging my boobs and nipples. My bare nipples. Oh. My. God.

I wanted to yell at him, to tell him to stop, that he had gone too far, that I couldn't do this. But...but...I couldn't. I didn't want to. It felt amazing, and was getting me really excited, and I didn't want it to stop.

Then Ethan took it even further. He leaned into kiss me, then bit on my neck and worked his way up to my ear. He licked my earlobe, flicking it with his tongue and gently pulling on it with his teeth, and whispered something.

Oh my god!

Ethan wanted to have sex, to go all the way.

But he didn't say it like that, where I could easily tell him no and push him off me. He was super sweet, and super sexy. He told me I was the hottest girl he'd ever seen, and that my kisses were magical. It was probably a line he'd practiced, but it didn't sound like one. I melted. And he never said sex or fuck like most people do. He said, "You are so beautiful and sexy, Carly...I wanna be a part of you; I don't think I can end this night without being inside of you, making love with you."

Before I could answer he kissed me again, and started touching me all over the place. It was so erotic, and I was delirious and confused; I couldn't speak, and didn't know what to say if I could. I didn't want to go all the way; I wasn't ready to lose my virginity. But I didn't want to stop, either. My heart was beating so fast, and I started sweating.

"I can't," I said, halfheartedly.

"Yes, you can," he said, kissing me, touching me more aggressively. His hands were roaming everywhere...squeezing my butt, caressing my thighs, working their way up to my private areas.

When I felt his fingers slipping inside the sides of my panties I quivered. "I can't," I said again. "I've never done this before."

"I'll be gentle, I promise," Ethan whispered. "You're so beautiful...I don't want this night to end without being with you."

He was so nice and sweet, and so deliciously sexy that part of me—a big part—wanted to just go for it. Losing my virginity like this, to someone so hot and perfect, might be worth it. But I was scared, too, more than I'd realized. I was also super turned on, and actually pretty horny, and probably not completely in control of my actions. I wasn't drunk, but had way more to drink that I anticipated, and was pretty buzzed—not that that was an excuse for anything.

Ethan and I continued making out for the next few minutes; he was kissing me, touching me, teasing me, and making me feel incredible—and then suddenly stopping and do it all over again. And then he'd ask again, just as I got to the point where I was most vulnerable. It was getting more and more difficult to turn him down. Finally, with one hand massaging my breast and pinching my nipple—oh god, how that felt!—and the other working the insides of my thigh, and his teeth nibbling and probably leaving marks al over my neck, he made his last plea.

"Oh, baby, I'm not gonna be able to stop myself soon," he said, kissing my neck, cheek and mouth.

"Then don't," I answered. "Don't stop. Let's just go somewhere more private."

Oh my god! What did I just say?

The two of us stood up and walked out of the room, holding hands. I was glad everyone was too busy to pay attention because it was obvious where we were going and why, and I was kind of embarrassed. Ethan led the way through the hallway into the kitchen, and then down a staircase to the basement. It was already empty down there, but we found a room off to the side...a TV room with a couch, a couple of end tables, and soft carpeting.

"This looks good," he said. "Nice and private."

Ethan sat down on the couch and pulled me onto his lap, kissing me, rubbing my shoulders and back, and pulling me tighter to him. I was getting into it, letting my fears and nervousness evaporate. If I was going to have sex for the first time, I was going to enjoy it. Then he pushed me forward, away from him, and grabbed each side of my shirt, quickly lifting over my head and tossing it to the floor. I sat on his lap like that for a moment, naked and exposed for the first time in front of a boy, my heart pounding.

"You look amazing," he said, grabbing me and pulling me into a kiss. We rolled around a little bit...touching, exploring. My insecurities of showing myself to Ethan were fading, and hey, why shouldn't they? I'd been taking showers completely naked in front of the girls at school since eighth grade, but with a boy it was different. And he was so cute and perfect. Then he stood up, unbuttoned his shirt, and threw it off to the side. With abs to die for, eyes to get lost in, and kisses like a god, I was a goner. He could have done anything to me and I wouldn't have objected.

He knelt down in front of me, kissing my belly and rubbing my boobs at the same time. His kisses began working their way upward until his mouth met up with his hands. He started licking and kissing my breasts...first the right one, then the left; then the right one again, and back to the left. He kissed them, licked them, and then bit me on the nipple...gently at first, then harder and harder. It felt incredible...so good at first, like a tickling/tingling sensation, then a deeper, more sensual and hotter/sexier feeling. I was moaning so loud I was worried people were going to hear me. I didn't care enough to want Ethan to stop, though.

But he did anyway. He stopped and moved back, targeting another part of my body. He took my legs and raised them above his shoulders, and started massaging my feet. He squeezed his hands around my toes, to my soles, and then to my ankles. He worked his way up each calf, rubbing, caressing and kissing. He was slowly making his way north, an obvious goal in sight. And as scared as I was, I wasn't objecting. I wanted him to get there.

Finally, he reached the place no one had ever touched me before, and started massaging my private areas over my jeans. It was better than I imagined, and I could feel the moistness in my underwear. When Ethan reached for the buttons on my jeans I didn't stop him, and lifted my butt off the couch so he could pull them—along with my underwear—off; he tossed them over his head and across the room.

And there I was. Totally naked, and completely vulnerable. Instinctively I squeezed my legs shut, but Ethan spread them apart with his hands.

"You are so hot," he said, staring at my vaginal areas, and in that moment I was both totally embarrassed and super excited at the same time. And I was thankful that the older girls in the locker room showers all shaved and teased anyone who didn't, because I wasn't hairy and gross when Ethan took off my underwear.

It started slowly. Ethan took his time, caressing my legs, my things, and moving higher and higher units his hands were on either side of my most private, sensitive area. Then he touched me...there. First with one finger, beginning at the bottom of my slit and sliding it slowly upwards. Once, twice, three times. Oh. My. God. It felt...wow. I don't even know how to describe it. On his fourth trip he stopped near the top, and began making circles with his finger on a spot—my clit—that felt so amazingly incredible. Once again I was moaning, begging for more.

"You're so wet, baby," Ethan said. "My sexy little virgin wants to become a woman, doesn't she?"

"Uh-huh," I said shyly. And then, to my astonishment, I added, "I want you to fuck me, Ethan."

"Ooh, you bad girl," he laughed. Then he licked me a couple of times. I squirmed at the sensation, both shocking and incredibly indescribable, sliding back and forth on the couch cushions.

Ethan slid his finger over my vaginal opening again, wetting it and then pushed it into my mouth. "You taste delicious, Carly, but I don't want you being a virgin for even one more minute."

He stood up and kicked off his sneakers, then unbuttoned his pants, pulling them, his boxers, and socks all off in one motion. His body...so hot, so perfect. I'd never seen a naked boy for real before, and it was better than I'm imagined. His member looked bigger than I thought it would, and part of me was terrified of it, while another part wanted to grab it and play with it. It was sticking straight out toward me, and I reached for it...excited to feel it in my hands, but only brushed it between my fingers when Ethan moved away. He was positioning himself—and me—for a better angle. With one knee on the couch, his other leg on the floor, Ethan spread my legs apart and moved himself closer.

"Are you sure you're ready?"

"Yeah, I think so."

Ethan maneuvered toward me with his manhood. I could feel the heat of his hardened penis against my vaginal lips. He slapped it against me a couple of times, then slid it over my slit, bumping into my clit. I moaned and giggled, both giddy with anticipated and frozen with fear. I closed my eyes and head my breath, and waited.

Then Ethan entered me, very slowly. I didn't feel the pain I was expecting, not the way Lauren and Becky had described it. It was both better and worse than I imagined, if that makes any sense. It didn't feel like the pain of getting hit or cut; instead it felt like my insides were on fire and being torn apart . With his first thrust, long and slow and deep, I hurt so bad I wanted to scream, to tell him to stop and never do it again, but I bit down on the insides of my cheeks instead. When he pulled back it hurt again, but I was able to let out my breath before he thrusted again. This time he went faster, and the pain singed my body so badly I groaned loudly, almost pulling my hips away from him.

"Are you oaky? Do you want me to stop?"
"No, it's okay. Keep going."

I can't tell you why I didn't ask him to stop. It hurt so bad that I had no idea why anyone would think this was fun. Stopping would have been so much better, but for some reason I wanted to keep going. It wasn't pleasurable at all, hurt way more than I thought it would, but I was also kind of turned on thinking about Ethan, and his penis inside of me. There was something about him—physically gorgeous, and really fun to be around—that excited me, and feeling his hard penis, its skin hot and pressing against mine, inside of me, was just so erotic and tantalizing that I didn't want to stop. We were like one person connected together, and that made me feel special.

After the first two big thrusts Ethan took, going all the way in and then almost all the way out—pulling it back all the way to the tip—he took a few shorter, quicker thrusts. That didn't hurt as bad, but didn't feel good either. It went on that way for a couple of minutes. He was saying something to me, but I wasn't listening; it hurt so bad I was clenching my teeth and trying not to cry. And I noticed I was a little bloody, too. Ewe.

"Are you sure you wanna keep going?"

I said I did, but Ethan stopped and pulled out anyway. "Let me see if I can find anything to help." He disappeared into a doorway on the other side of the room; I heard some running water, and then a moment later he returned with a small bottle and some toilet paper. "Well, your tight little pussy's no longer a virgin," he said, wiping up the mess he'd created. "And this should help...if you wanna keep going?"

Ethan squirted some baby oil onto me, at the top of my clit and let it drip down onto my pussy lips. His fingers making small circles on my clit felt amazing, and I began relaxing, unclenching my teeth. "Do you want me to fuck your cute little pussy some more?"