My Friend Taught Me to Stop Being Afraid of Anal Sex

For those of you who’ve been reading what I write, I know many of you are curious to know how my first time from behind went. Today isn’t the day for that whole story; I’ll leave that for later. What I do want to tell you is how Renata, a twenty-three-year-old girl who was in my classes at the university, ended up being the person who got the fear out of me, and I’m going to give you, at the end, an explicit preview of that night.

Renata was two years behind the rest. She had dropped out of the degree, then come back, and that’s why she was a few years older than almost everyone else. She was gorgeous: dark-haired, tall, with Andean features, thick lips, and legs that seemed to go on forever. An exotic beauty who, on top of that, carried a horrible reputation. They called her “the easy girl” with a cruelty I didn’t bother to question at the time.

One afternoon I was with my boyfriend in my room. We’d been together for two years, we’d already lost our virginity to each other, and we got along too well. What we had didn’t seem like a relationship between nineteen-year-olds: there was a maturity that let us talk about anything without jealousy or awkwardness, and also a constant horniness that made us fuck in every gap we found, in my room, in his, in the car, against the bathroom wall in someone else’s house. His hard cock and my wet cunt were, by then, a language we spoke fluently.

That afternoon we started talking about fantasies. No filter, the things we’d like to try. I went first. I confessed that the idea of doing it outdoors, under the moon, really turned me on, and also in some public place where we could get caught. Just imagining it made my pulse race and my panties get wet.

Then it was his turn. He talked to me about my feet, about how he’d love for me to stroke him with them, to paint my nails a dark polish. Things that, deep down, weren’t so far from what we were already doing. And that’s when I suspected he was hiding something from me.

—Is that all your fantasies? —I pressed.

—…Yeah.

—You sure? I think there’s something you don’t want to tell me.

—Well, yeah. There’s another thing. But it’s kind of hardcore.

—And you weren’t planning to tell me?

—You’re not going to get mad?

—No. That’s why I’m asking.

He was quiet for a second, as if weighing the ground.

—One of my fantasies is fucking you in the ass. When we fuck doggy style I look at your little hole and I get rock hard. Besides, there’d be nothing to worry about.

—That’s an advantage —I laughed, nervous—. Anyway, with the cock you’ve got, you’re going to split me in half.

It wasn’t entirely a joke. He was, within normal bounds, quite a bit thicker than average, and I was terrified he’d hurt me. Terrified, and a little ashamed of messing him up or messing myself up.

—We’d do it carefully —he said—. Anyway, Damián told me he did it with Renata and that she loved it, that she asked him to shove it all the way in.

—Renata? The one they say screws anyone?

—The same one. Don’t tell me you’re jealous?

—Not at all. I’m curious why he takes it for granted that because she likes it, I’m going to like it too.

—It was just a comment. Relax, she doesn’t interest me.

The truth is that, yes, I did get jealous. Imagining that my boyfriend had thought of her that way made me uncomfortable. But it was my problem, and I had to solve it myself.

***

The thing is, Renata stayed on my mind. I wanted to talk to her, get to know her, understand why she carried that reputation without seeming to care. The only thing we shared was gym class, so that was my only ground for getting close.

The following week I ran into her on purpose and it went terribly. I nudged her by accident on purpose and almost made her fall.

—What the hell are you doing, bitch? You could’ve hurt me.

—Sorry, I didn’t see you. It was an accident.

—Be more careful next time.

It had gone badly, but it had given me a golden opportunity: to make it up to her. I bought her a soda and something to eat, and at the end of the next class I gave it to her.

—Hi, Renata. I wanted to apologize for the other day. I didn’t mean it.

She opened her eyes wide, surprised by the gesture.

—Uh… thanks. You didn’t have to.

—I really felt bad about it.

—I’ve got nothing to do for another hour. Want to have it together?

—You don’t mind?

—Not at all.

—I’d love to, then.

We talked for about two hours. We missed the next class and didn’t care. We left there practically as friends. I added her on all my socials and, little by little, what we had turned into a real friendship.

***

Some time later, at my house, I gathered my courage and asked her about her reputation. It seemed incredible to me that such an intelligent woman could put up with it so calmly.

—It’s partly true and partly nasty bullshit —she told me—. When I broke up with my ex, he started spreading rumors and even posted intimate photos I’d taken for him. Since I gave them to him and I’m an adult, nobody could do anything. He wrecked me. After that, yes, I fucked several people, all adults, all consensual. Why should I care what people who don’t even know me say?

—Of course. Not at all.

—Exactly. And let me make two things clear. I don’t use words that punish the sex a woman chooses to have. And that ex didn’t just ruin my reputation: he abused me. For me, fucking is also about taking back control of my own body.

—Sorry, I didn’t know.

—You don’t have to apologize or have known. Now tell me, what do people say about me out there?

—That you sleep with professors for grades. That you sucked Nacho off in the bathroom. That you’re into girls. And that you had a threesome with two guys.

—And do you believe all that?

—I don’t know. It’s what people say.

—With professors? Never. If that were true, I wouldn’t be behind, would I? The Nacho thing is an idiot who couldn’t resist showing off in front of his friends: yes, I sucked his dick one night in a club, and I swallowed it all, so what? I kissed a girl and did a bit more at a party, with Camila, is that such a big deal? The threesome is true. I had one cock in my ass and another in my cunt at the same time, and I loved it. Any problem?

—No. Not at all.

I felt uncomfortable, but not because of her. Because of me. I had no right to have judged her the way I had, especially because I also wanted to try anal, and I also got insanely turned on watching videos of women with two men, rubbing my clit until I came clean while I watched them on the computer. Without realizing it, tears filled my eyes.

—What’s wrong, Juli? —she asked, using the nickname she’d already given me.

—I feel bad for having judged you. You didn’t deserve it.

—Don’t worry. You’re still young, you need more street smarts. Men think they own the right to tell your business like it’s theirs.

That afternoon we hugged. She told me about her experiences, but like an older sister, so I wouldn’t trip over the same stones. I was moved for days.

***

Time passed, we kept hanging out, until one afternoon the moment I’d been looking for finally came.

—Lu, I want to ask you something intimate. Can I?

—Obviously. We’re friends. At least I consider you a friend.

—I consider you one too.

We hugged.

—What did you want to ask me?

—My boyfriend told me he’d like to fuck me in the ass. And since you’re the only person I know who’s done it, I wanted to ask you.

—Uh-huh. Yes, I’ve done it several times. But what’s the actual question?

—I want to know how to do it and, above all, how to enjoy it.

—Okay, let’s start. Do you trust your boyfriend?

—With all my heart. He’s always respected me, he never goes around telling our stuff, my family adores him and his family adores me.

—Then you already have the first step, which is the most important: trust in the person beside you.

—That makes me feel better.

—Anal can be catastrophic or it can be the best thing that ever happens to you. With my ex I ended up in the ER. With another guy I had orgasms that made me see stars. The difference is in how it’s done.

—And what’s the difference? Can you explain it in detail?

—Take notes. The ass is a muscle that stretches, but it doesn’t lubricate itself, like your cunt does when you’re horny. If you don’t give it time to open up and don’t lube it well, you earn fissures, tears, ugly pain. Now, if you stretch it slowly and patiently, it can be incredible.

—And how do I start?

—First, a talk with your boyfriend. The yeses, the nos, when to stop, when to keep going. You have to be one hundred percent sure he’ll stop the second you say enough, even if his cock is about to explode.

—I’m sure of that.

—Then, lubricant. A lot of it. Good quality, silicone-based. And don’t be disgusted by your own body: you’re having sex through a place that is what it is. The only thing you can do is eat light that day and drink water. The rest is part of the game. You’re not filming a porn movie.

—It’s just that I’m embarrassed.

—Embarrassment is part of sex too. You’re naked with another person, sweating, with smells, with a mouth full of semen, with someone else’s fingers inside you, with everything. Get over it. Nobody’s perfect in bed.

—No one’s ever spoken to me with such honesty.

—Relax, Juli. I’m here to help you.

—And how do I keep going?

—I’m not going to give you position tips; you’ll figure that out yourself. I’m going to explain how to prepare the body. The first thing can be done by you or your boyfriend: lube up a finger and slowly penetrate your little hole. You’ll feel pressure, but you get used to it fast. After a few minutes, switch to a thicker finger. And so on.

—And then?

—You keep going up in size slowly, without rushing. Two fingers, you or him. If it really hurts, stop and continue another day. It’s fine. You’re never completely ready, and that’s okay.

—And how do I know if I’m ready?

—By learning to read your body. Burning usually means an injury: stop there. Dry pain means the muscle is too tight: relax and breathe. Discomfort is normal and goes away with practice.

—And when that moment comes?

—That’s when he puts it in, very slowly, just the tip of the cock at first, with tons of lubricant. And he stays still so you can get used to having it inside. The first few times it’s hard, but you shouldn’t feel pain. Discomfort, yes. Pain, no.

—And is it really enjoyable?

—With practice, yes. The ass is full of nerve endings. I’ve had orgasms with just a cock in my little hole, without anyone touching my clit. But I’ve also ended up bleeding on an exam table. For me, anal ranges from the worst to the best thing I’ve ever experienced. If your boyfriend does it right, and you explain how and when, I assure you the relationship between you two will grow.

—I’d love for that to happen. I trust him.

—I’m glad to hear you say that. I hope everything goes well. And tell me when it happens, huh? —she laughed—. I want to know if I trained you well.

—Obviously. You’ll be the first to know.

***

Time passed, and one Saturday night I knew it was the night. I ate light, drank water all day, bought the lubricant Renata had recommended, and left it in the drawer of the bedside table along with a couple of dark towels. I shaved completely. I put on a black pair of panties and a long T-shirt without a bra. When he arrived and closed the door, he found me already trembling, my hard tits pressing against the fabric.

—Are you sure? —he asked, grabbing my waist.

—Yes. But remember: if I tell you to stop, you stop. Even if you’re about to come.

—I swear it on whatever you want.

We started kissing while standing against the door. He shoved his tongue all the way into my mouth and I felt my knees go weak. His hand slid up under my shirt and squeezed a breast until I moaned. He pinched my nipple between two fingers, tugging just a little, and I was already feeling his cock rock hard against my belly, pushing under his jeans. I started stroking him through the fabric while he pulled my panties down with his other hand and drove his middle finger into my cunt, which was already dripping.

I took him to the bed, pushed him onto his back, and unbuttoned his pants. I pulled his jeans and boxers down in one yank. His cock stood up in front of my face, thick, the vein standing out, the tip already shining with liquid. I grabbed it with both hands and ran my tongue from his balls to the glans, slowly, looking him in the eyes. He let out a “holy fuck” that made me laugh with my mouth open.

I started sucking him like he was the last dick on earth. Mouth wide open, drooling on myself, taking him down my throat until my eyes filled with tears and mascara ran. He grabbed my hair and set the rhythm, pushing my head downward. Every so often I’d pull back, spit on him, and rub him against my face, against my cheeks, against my tongue. I licked his balls one by one while working his cock with my hand, and he writhed on the bed, biting his lip so he wouldn’t come in my mouth.

—Stop, stop —he said, hoarse—. I want to come somewhere else today.

He ripped my shirt off in one pull, threw me on my back, spread my legs wide, and dove headfirst into my pussy. He started eating me like he was truly hungry, with his whole tongue, sucking my clit until the whole bed started shaking with me. He put two fingers in me and curled them inside, searching for the spot he already knew by heart, while with his other hand he squeezed one breast. He made me come like that, with his tongue planted on my clit and his fingers buried to the knuckles, and I screamed into the pillow so much my throat hurt afterward.

When I came down from the orgasm, my cunt still throbbing, he lay on his back and motioned for me to climb on top. I straddled him, rested the tip of his cock at the entrance to my cunt, and slowly started taking it in, feeling how it opened me little by little from the inside. I started moving, riding him, with my hands on his chest. He watched my tits bounce and squeezed my hips, setting the pace. We fucked like that for a long while, unhurried, so I could finish loosening up. Another orgasm, smaller but deeper, shook me when he sat up and hugged me, never stopping thrusting from below, his tongue between my breasts.

—Do you want to keep going with the other thing? —he whispered in my ear, sweaty.

—Yes. But get me ready yourself. Like I told you.

I lay down face down, with a thick pillow under my hips and my ass raised. He took the lubricant out of the drawer and squirted a generous amount onto his fingers. I felt the cold against my little hole and shivered all over. With his other hand he stroked my back, my hair, my waist, trying to calm me.

—Take a deep breath —he said.

He slid his middle finger in, very slowly. It was a shock. Not pain: pressure, invasion, something forcing its way into a place where nothing had ever gone before. The muscle resisted and another part of me said yes, keep going. He stayed still for a second, then started moving it in circles, in and out with patience. After a minute I was already liking it and I pushed my ass against his hand, asking for more without words.

—Another one —I whispered.

He put his index finger in alongside the middle one. That made me moan louder, my mouth against the sheet. He worked his way in with more lubricant, adding more and more each time, until it stopped hurting and started to feel weird-good, a sensation I’d never had before in my life. He spread his fingers inside me, scissoring me open, stretching me. With the other hand he reached around underneath and started rubbing my clit at the same time. The combination drove me crazy. I’d never felt my cunt and my ass throbbing together like that, as if my whole body had become one single hole begging for cock.

—I need you to put it in already —I told him, my voice already hoarse.

—Not yet. A little longer.

He listened to Renata without ever having heard her himself. He worked me with two fingers, then three, until the muscle gave way completely and I was left open, wet, panting against the sheet with my ass raised like a cat in heat. Only then did he lube up his cock —an excessive amount, dripping down his balls onto the sheet— and position himself behind me. I felt the hot tip rest against my little hole and my whole body tensed again.

—Relax, baby. Just the tip. If you want it out, it comes out.

He pushed with a calm I didn’t know he had. I felt the sting of stretching, the tip forcing its way in, and I breathed deeply like she’d told me, letting the air out slowly. It didn’t hurt. It stung a little, but it was bearable, even nice within the sting. He stayed still, with only the tip inside, not moving a millimeter. He stroked my back, spoke to me softly, told me I was beautiful, while I got used to the sensation of having a cock in my ass for the first time.

—Are you okay?

—Yes. Put it in a little more.

It went in millimeter by millimeter, with infinite patience. Every so often he stopped. Every so often he added more lubricant. When he was all the way inside me, his balls pressed against my cunt, I felt a fullness that had no name. It wasn’t pain. It was a new intensity, as if he were opening up a space inside me that I hadn’t known existed.

He stayed still for a long while before starting to move. He pulled it out just a little and pushed back in, with a slow pace that was both maddening and beautiful. I started moving my ass against him, asking for more, and he gradually picked up the rhythm, coming almost all the way out and spearing me again to the hilt. He grabbed my hair, yanked my head back, and sank his teeth into my shoulder.

—Holy fuck —I heard him say, voice wrecked—. You have no idea how much your little ass is squeezing my dick.

—Fuck me harder —I begged, surprised at myself—. Tear my ass up, come on.

He slid his hand underneath and started rubbing my clit again, never stopping pounding me from behind. With two fingers of his other hand he filled my cunt too, and there I felt total madness: his cock in my ass, his fingers in my pussy, and his thumb on my clit, all at the same time. The combination was devastating. I felt something different building up in me, something deeper, rising from a place in my body I didn’t know. I started moaning without being able to stop, whispering filthy things in his ear, begging him to split me open, to fill my ass with cum, not to stop ever. Things I’d never said out loud before.

—I’m about to come —I yelled into the pillow.

—Me too, baby. Inside?

—Yes. Inside. All of it.

The orgasm hit me like an earthquake. My whole body pulling inward and outward at the same time, my ass squeezing his cock in spasms as I convulsed all over. He held out for two or three more thrusts, growled like an animal, and unloaded inside me, and I felt every beat of his cock in my little hole, every gush of hot cum emptying into my ass, while I kept trembling under him with my fingers clenched in the sheet.

He collapsed on top of my back, sweaty, panting, his heart pounding between my shoulder blades. He stayed inside me for a long while, until his cock softened and slipped out on its own, with a wet sound that made me feel embarrassed and tender at the same time. I felt the warm thread of semen running down my thigh. I felt empty, but empty in the best possible sense, as if he’d left me a warm hollow that belonged to me alone.

We stayed wrapped around each other in silence for a good while, legs tangled, him stroking my hair. Then we went to take a shower together. Under the hot water he hugged me from behind, his cock still soft against my ass, and told me in my ear that he loved me, that he thanked me for trusting him. I told him I loved him too, my voice breaking, and burst into tears of emotion against his chest.

That night I slept like I hadn’t slept in years, with the feeling that I had crossed a door that would never close again.

The next day I called Renata and told her everything in vivid detail, every finger, every inch, every moan. She laughed, congratulated me, told me I’d been an excellent student. But that conversation, and everything that came after between her and me, are also other stories I’ll keep for later.

For now I’ll tell you that, a year later, Renata left backpacking and now lives up north. We write each other from time to time and I miss her a lot. She’s the older sister I never had, the one who taught me that fear almost always comes from not daring to ask.

If you feel like it, another time I’ll tell you her own stories, the good ones and the hard ones, because there’s one in particular —that threesome that marked her so much, with two cocks fucking her at the same time— that’s one of the hottest things I’ve ever heard in my life. I hope you liked it. Don’t forget to leave your comment.