[FM] I lost my anal virginity on prom night…and it was awesome

*Note: All the people in this story were 18 at the time of writing.*

On the few occasions that i’ve told this story to people, it always, undeniably, elicits a laugh. “You *what?*

“I lost my anal virginity on prom night,” I’ll repeat, laughing.

“I know, but…girl, you are brazen.”

Indeed, I am. And I was, even back that. That’s probably one of the reasons my ex, and my first-ever boyfriend—let’s call him Diego—as with me. We had *fun*, everywhere we went. Since we met in high school, we had to get creative about the places where fun was to be found. That meant parking the car at “our street,” or meeting at “our park” at night, or taking long hikes in a nearby nature preserve and hoping there wasn’t a family with toddlers rounding the corner or something much, much worse (luckily I hadn’t seen *Mindhunter* back then and wasn’t as outright paranoid as I am today).

I’d lost my “conventional” virginity to not long into dating Diego. You know how some girls in high school tease their virginity for a while and make their boyfriends wait? Yeah, not me. Probably because it was the second semester of my senior year, and I was crazy about him, and *not* listening to my body definitely felt worse than listening to it would. We were sitting outside, having taken a break from a school dance, and I more or less told him that I wanted him to fuck me. After that, it didn’t take long.

The next year, I was in college, and he was a senior in high school. I returned to our town to be his prom date—I know, very devoted. But by then we were a *couple*. Had gone through *stuff*. Had done *long distance* (even if it wasn’t *that* long distance). After all that, prom was a cute event. But how to commemorate it? I guess what I mean is, it was time to try something different, at this event which symbolized the culmination of so many years and hard work.

But anal? That wasn’t the plan. There *wasn’t* a plan. The only plan was me leaving classes early, putting on a white dress that I bought off an internet ad because I didn’t want to go prom dress shopping as a freshman in college, and showing up back to our hometown half an hour away from my university.

Taking prom pictures and returning to the hotel where my own prom had taken place was eerie. It was like going back in time, or trying to fit back into my older self. But the fit wasn’t right. It was scratchy. I was different, now.

Still, Diego and I worked. That hadn’t changed. Maybe we were even better than we were last year, because we spent our weeks apart and were always happy to see each other when we could. At prom, my boyfriend and I spent most of the time on the dance floor. Our bodies loved being around each other.

“Thank you for coming, ‘he said, as we danced, knowing that I was the only one of my year who had returned for his class’s prom.

“Thank you for inviting me,” I said.

“Are you nuts? I’m proud of having a sexy older girlfriend,” he said, laughing. In reality, I was only a few months older than he was. By then, we were both 18. “I want to show you off.”

We stayed glued to the dance floor for a while. Unfortunately, while I had a great reputation in high school and my teachers loved me, I had a terrible reputation at school dances and my chaperones hated me. My boyfriend and I, simply put, could not keep our faces away from each other. Like magnets, we made out and then separated and then made out again. I *knew* PDA was generally frowned upon by adults. I *knew* I was an adult. But I was also young enough to think that if I didn’t kiss him as passionately as I wanted to, right then, I’d combust.

Part of the problem, I think, is that most of our relationship in its nascent stages was spent outrunning both sets of super-strict immigrant parents. There was nowhere that we could comfortably and safely be together within our houses. So, we had to be creative and find spaces out in the world—including dances. Our teachers couldn’t ground us for being human, and kissing each other. Our parents, however, could. And did.

Now, at least, I was in college, and we had experienced the nirvana of my single bed. It made me—made us—reckless. It was 11pm when prom ended, and I knew my parents would be asleep. Most of his class was headed down the shore as per our high school traditions. But—see: immigrant parents—we were never allowed to partake in that three-day-long unsupervised orgy (yes, pretty much literally).

“Want to go to my house or the diner?” I asked, as people were shuffling out of the hotel ballroom. We’d spent many late nights speaking to an old waitress at the local diner, who brought us huge slices of cheese cake and gave us that, “You crazy kids!” wink.

“Your house,” he said, roughly, adjusting his tuxedo. “I need to get outta this thing.”

So I drove us home. To this day, I don’t think he ever learned to drive. Maybe all my chauffeuring was bad, after all. The house was dark when we walked inside, which meant that we could go to the basement. However, that isn’t what happened. Since we had free reign, we started making out on the couch in the living room, right under my sleeping parents’ bedroom.

“Wait,” I said. “Let me get changed.” The white dress was gauzy and catching everywhere.

“No,” Diego murmured.”Take it off.”

“Take it off?”

He nipped at my lips, playfully. “Take it off.”

I stood up and he unzipped me until I was naked. There was a thrill to be so exposed in my house, but also a terror. Because this was a bad idea. Irresponsible. Disrespectful. Ridiculous, when the basement was right there, and at least then we’d have time to find a blanket if the big bad wolf came down without notice, as had happened before.

But he kissed my neck, and the dress was in a pile on the floor. “Just for a little,” I said. “Then we’re going downstairs.”

His fingers traced my nipples, tweaked them. “Sure,” he said. Not convinced.

He didn’t take off his boxers. Instead, he nestled his thin, warm body around mine and we kissed and kissed. Lately, we’d been exploring how much I loved my asshole to be fingered while he fucked me. It was a feeling of exquisite fullness, like he totally owned and dominated everything that had once been open. Making out, he reached around and ran his fingers over my asshole.

“You like that, don’t you, Len?”

I blushed. “You know I do. Don’t make me admit it.”

“Don’t make you admit what?” He leaned over, whispered in my ear. “That you’re dirty as fuck?”

“Yeah, that,” I said, writing under him. Then he put his finger in farther, so that instead of grazing, it was puncturing the front of my tight asshole. I exhaled, relaxed. Let him in more.

“I love that,” he said. “I love you for loving it.” Then I relaxed even more, and his whole finger went inside of me, for the first time. I exhaled, and felt as he made circles there. “Do you like the way this feels?”

I murmured as an assent. I didn’t know if I liked it completely, but I was on my way to liking it. And I liked how much *he* liked it.

“You know what I want to do for my graduation present?” he asked. “And prom night, and everything, all in one?”

“No, I’m not going to give you a lapdance,” I said, laughing. I am not a good dancer.

“No, babe. Think about it.” He wriggled his finger in my asshole more and we made eye contact.

“Now? You want to do this *now*?” We’d spoken about it but always in the abstract, never making plans for attempting to insert his cock into my asshole. Which normally, requires planning.

“Yeah,” he said, propping himself up so he could take a better look at me. “Let me.”

“Fine,” I said, but I was scared that if I moved or did anything, I’d lose my bravery.

A brief detour: Nothing that I’m about to describe is a good idea. If you’re going to have anal sex with someone, don’t do it like this. Do it somewhere private, where you can handle if things go unexpectedly. Do NOT do it on your parents’ couch.

Bur I probably wouldn’t have taken my own advice. I knew better even then, and ignored it. I brought down a towel and a tiny bit of lube that I managed to have in my childhood bedroom. “Told you. Incorrigibly dirty,” he said.

He laid me down on the towel, like I was losing my virginity again. We made our first attempt, with him inserting himself as we stared at each other. But I kept clenching. There’s no way it was supposed to feel this painful, I thought. Nothing about it felt right.

Some days, it doesn’t ever feel right, I’d learn later. Some days, it would. This turned out to be in the second category.

He turned me around so that I was on my knees. Then he played with my hanging tits for a while, which I love, and fingered my pussy from behind, which I also love. “God, you’re so loud. Do you hear your pussy right now?” It was making squelching noises as he rammed his two fingers in and out of me. “Maybe I should just fuck you here. You clearly want me in your pussy.”

“No,” I found myself saying. “I want your cock inside of me. Inside of my asshole.”

“Oh, really?” His finger traced my puckered hole again. I slumped down farther, unable to sit up completely straight from desire. He pushed his wet finger in further, in and out.

“Yes,” I murmured.

“Your asshole wants me too,” he said. “I can tell. Look at how you’re taking me right now.” I moved my hips back and forth to show that he was right, that I wanted him. “I’m touching my cock with my other hand, babe. I’m getting it ready for you. It’s gonna feel so good.”

“I’m ready,” I said. I didn’t know if I was, actually, but I wanted to try. He leaned forward. I felt his hot chest against my back. He was fumbling with the lube, trying to find a way to keep everything neat as we were about to do something very, very dirty.

He started fingering my asshole with two fingers, opening me up further “God, babe, you’re doing so well. Look at those two fingers. You’re getting all stretched out for my cock. I know it’s big, but you can take it. Do you want it?”

Yes, I murmured. Yes.

“Good,” he said, positioning himself at the start of my hole. He kept moving his fingers in and out and then removed them, but seamlessly put the tip of his cock in its place. He had a gorgeous, thick, seven-and-a-half long cock. My favorite yet. It hit every spot.

I leaned down farther into the couch, dragging the drool where I opened my mouth and moaned loudly. “Oh my god,” I said. I couldn’t describe the feeling of fullness, but I wanted more.

“Are you good?” he asked.

Head buried in the couch, I nodded. “Keep going,” I said.

He grabbed onto my hips and pushed in gently. Millimeter by millimeter. My asshole grew to accommodate him he reached around and fingered my clit so that at least there would be conventional pleasure mixed in with this strange sensation that i hadn’t the words for. As he pushed in, It was all I could do not to scream. This felt weird, like pushing something in when I normally pushed things out. It felt wrong. My body was rebelling.

And then finally, he was inside me. He didn’t move. He told me to relax. “There’s nothing else to put in, baby. I’m here.”

I relaxed around him, and his cock started to move in and out with the freedom. He groaned, even though he was out in the open air of my living room.

Then, next thing I knew, his fingers were inside my pussy. I was full again, back to that fullness. And somehow, it felt better than ever. This was like heaven. Did I love anal? Was I discovering that, in this moment? It was a lot to process, so I just rode the wave of newness, experiencing every plunge of his cock into my asshole like it was the first time.

We were silent, after that, letting our bodies and instinct take over.

Eventually, he asked me if I wanted to come. “Yes,” I murmured.

“Because I want to feel your asshole clenching when you come around my cock, baby. I want that for my present.”

I groaned into the green fabric couch. This was going to be a drool disaster. He reached around and started fingering my clit. Instead of moving, he lay down on top of me, and left his cock buried inside me. Slowly, he ran his fingers around my clit in circles, the way I do to myself most mornings (and evenings).

In my ear, he started whispering a stream of smut. *You’re my dirty slut. No one else’s. You gave your asshole to me, babe, and now you’re all mine.* I writhed around on the couch, bucking against his cock, his fingers. “Put your fingers inside me,” I said. “I’ll do the clit.”

And that’s how I came. His fingers and cock in both of my holes, and me hungrily fingering my pussy. As the waves of pleasure spread around my body, making me shudder, he shuddered too.

“Oh my god,” he said, “That felt so good. But I want to fuck your pussy now.”

He went to the sink and washed his cock clean. Then he came back. “Stay like that. On your knees. I like the view.” He slid into my pussy so easily, and I was reminded that the other place was fun, but this was his home. I immediately arched my back and he caught me, raising my torso up so that we were both upright on our knees, and he was holding me.

He bit my ear and kept thrusting upwards, upwards. “I”m going to come,” he said.

I begged for him to come, and then he did, finally. I was on the pill and didn’t want him to come inside me most nights, but this was prom night.

“Good thing you put a towel down,” I said, watching his cum drip out of my pussy and onto the tan towel.

“Let’s go downstairs before we get caught,” he said, laughing.

“*Now* you say this?” I asked.

“The getting caught was part of the fun,” he said, and I playfully called him a monster.

We didn’t put our clothes back on, but bundled the dress and the towel together and ran downstairs, where we held each other and laughed and talked about the future. He was joining me in college a few months later. At that point, we couldn’t imagine anything breaking us. At that point, nothing could. Things changed, but I’ll never forget the level of comfort we had with each other, and the bold and honest communication we always practiced. If it hadn’t been for those already established values, plus a lot of luck. I think the prom night anal story might have a wildly different outcome. Because y’all: It could’ve been a disaster. Instead, it has become a treasured memory.

And if you’re reading this, out there—thank you.

Source: reddit.com/r/gonewildstories/comments/i0lv3i/fm_i_lost_my_anal_virginity_on_prom_nightand_it