My Friend Wanted to Get Over Her Fear of Anal Sex

My name is Martín, I’m in my early forties, and for some time now I’ve said openly that I’m bisexual. I wasn’t always so clear about it. For years I kept it to myself, even when I was married to an intelligent, open-minded woman, Natalia, who ended up leaving me shortly after I confessed it to her.

I’m not going to pretend to be delicate: I like women, I like men, I like cunts, asses, and cocks. With men I’ve almost always been passive, and that taught me quite a bit about anal sex: when it hurts, when it feels good, when the body closes up out of fear, and when it opens because desire wins out.

I’d also been with women who enjoyed being penetrated from behind, but I never imagined that experience would end up becoming important to Clara, a coworker I’d been friends with for years. Clara was attractive, one of those women who don’t need to provoke anyone to draw attention, but for a long time I saw her as a close friend, almost a confidante.

One afternoon, during lunch, I worked up the nerve to tell her about myself. It wasn’t some grand dramatic scene: we were sitting at a secluded table, with bad office coffee and the murmur of everyone else in the background. She listened to me in silence, blinked a couple of times, and smiled.

“The truth is, I always suspected it a little,” she said.

“Why?”

“Because you look at things differently. I don’t know how to explain it. But I’m glad you told me.”

The conversation continued with ordinary questions: when I’d realized it, whether it had been difficult to accept, how my ex had taken it. Until Clara lowered her voice, toyed with her coffee spoon, and turned red.

“When you’re with a man... what do you do?”

“You want to know whether I’m active or passive.”

“Yes. That.”

“Almost always passive,” I replied. “Sometimes active, but less often.”

Clara’s eyes widened with a mixture of surprise and curiosity. There was no mockery on her face. There was a much more intimate question caught in her throat.

“And doesn’t it hurt?”

“Not anymore, hardly ever. It did at first. I learned to relax, not to fight my body.”

Then she told me what was really troubling her. Her partner at the time, Iván, had been insisting for months on penetrating her from behind, and she always refused. Not only because she was afraid of the pain, but because of shame, because of that idea that the ass was a dirty, awkward, dangerous place.

“I’d like to talk about this over a drink,” she said, trying to laugh.

We made plans to meet after work.

***

We didn’t go to our usual bar. We walked several blocks until we found a dark, quiet place, almost empty, where no one from work could interrupt us. We ordered two beers and sat at the back, at a small table that forced us to talk close together.

Clara started by thanking me for trusting her, but she soon returned to the subject. She told me that an ex, Daniel, had once tried to put it in her from behind without any care and had hurt her terribly. Since then, she associated anal sex with pressure, pain, and humiliation.

“And now Iván is bringing up the same thing again,” she said. “Sometimes I think they all end up getting tired of me because of it.”

“Don’t be ridiculous. If someone leaves you because you don’t want to try a particular act, he’s the one with the problem.”

She stared at her glass. Her eyes were shining. To take some of the weight off her, I explained simple things: the importance of going slowly, using lubricant, starting with fingers, letting the body set the pace. I also talked to her about cleaning, because that was an obsession of hers.

“Can you really feel at ease about that?” she asked.

“Yes. It isn’t complicated. And above all, it isn’t anything to be ashamed of.”

She ordered another round, two gin and tonics this time. The conversation became more direct. She asked me about my first time with a man, and I told her enough: a gay bar, an older guy who read my face, a night when the fear didn’t disappear, but lust shoved it into a corner.

“Did you come even though it hurt?” she asked.

“Yes. A lot. Pain wasn’t the only thing I felt. There was desire, shame, curiosity, brutal arousal too. In my case, my prostate did its part as well.”

Clara swallowed. The word “arousal” changed her breathing. Just then she looked at her phone, and her face hardened. She read one message, then another, and placed the phone facedown on the table.

“Iván just dumped me,” she said. “By text. How elegant.”

I hugged her without knowing what to say. She didn’t cry much; she stayed still against my chest, with a cold anger tightening her jaw. Then she pulled away, took a long drink, and gave a bitter laugh.

“It’s over. I’m not going to keep feeling broken because of this. I want to learn.”

“Clara, you’re hurt.”

“I am hurt, yes. But I’m not out of my mind. I want you to teach me. Who better?”

I looked at her seriously. There was alcohol, spite, and a friendship that could change forever. Even so, her voice didn’t sound impulsive. It sounded determined.

“We can talk tomorrow,” I suggested.

“No. Tomorrow I’ll be embarrassed and hide again. Tonight I want to put an end to this.”

We paid. On the street, before we reached my building, we stopped at a pharmacy. I bought an enema bulb, and she waited outside, smoking without lighting the cigarette, simply holding it between her fingers.

“Is that for me?” she asked when I came out.

“So you can feel at ease. That’s all.”

We went up to my apartment in silence. In the elevator she took my hand and kissed me quickly, almost awkwardly. It wasn’t romantic. It was a declaration of nerves.

***

At my place I explained how to use the bulb with lukewarm water and lubricant. I didn’t make a spectacle of it or turn it into cheap titillation; for her, it was important to strip that part of her body of its burden of filth and fear. She shut herself in the bathroom, and I stayed in the living room, my cock hard inside my pants and my head full of doubts.

When she came back, she looked different. She wasn’t falling-down drunk or absent. She was nervous, yes, but aroused too.

“I feel strange,” she said. “As if I’ve crossed a door.”

“You don’t have to do anything else if you don’t want to.”

“I want to. And I want you to stop treating me like I’m made of glass.”

We went to my bedroom. I took out lubricant, a small plug, and two toys of different sizes. Clara stared at them with a mixture of fear and desire.

“You start on your own,” I told her. “One finger, slowly.”

She took off her clothes without putting on a seduction act. Blouse, pants, bra, panties. Her adult body was left beneath the warm light of my lamp, real, beautiful, with the kind of vulnerability that needs no posing. She lay facedown, parted her legs slightly, and looked back.

“Don’t leave.”

“I’m here.”

She put lubricant on her fingers and carefully caressed the entrance to her ass. I watched her shudder when her index finger began to go in. It wasn’t quick or effortless like in an automatic fantasy; she took a deep breath, frowned, stopped, and tried again.

“It’s strange,” she murmured. “But it doesn’t hurt.”

“Keep breathing.”

She moved her finger slowly, pushing it in to the knuckle and barely drawing it out, as if she were learning a new language. With her other hand she touched her cunt. At first it was almost a reflex, but as soon as she brushed her clitoris, she let out a low moan.

“I’m wet,” she said, surprised.

“I can tell.”

“You do it.”

I sat beside her. I covered her fingers with more lubricant and rested one hand on her buttock, without rushing her. First I slipped in one finger. Her ass was hot, tense at the beginning, and then it began to yield around my finger with small spasms.

“That’s it,” I whispered. “Don’t fight the pressure.”

Clara buried her face in the pillow. When I added a second finger, she let out a long whimper, more from surprise than pain. I began moving them in slow circles, opening her little by little, feeling how the lubricant made each entry glide smoothly.

“Fuck,” she said. “It feels full.”

“And I can still go more slowly.”

“No. Keep going.”

With my other hand I stroked her thigh, then her waist. She continued touching her cunt, with less and less shame. Her fingers moved quickly over her clitoris while mine worked her ass patiently, going in and out, widening it without roughness.

When she accepted the third finger, her back arched. The pressure was greater, more like a cock. I kissed one buttock, then the other, and she laughed with a tremulous sound.

“Now I understand why you talked about lust.”

“Lust helps.”

“I don’t want the toy,” she said. “I want you.”

I stripped with an urgency I could no longer hide. My cock was hard, heavy, and gleaming with lubricant when I positioned myself behind her. Clara spread her legs wider and grabbed the sheet.

“Slowly at first,” she requested.

“Slowly.”

I pressed the head of my cock against her asshole and pushed just a little. The first resistance was firm. She inhaled sharply, dug her fingers into the bed, and I stayed still with only the tip inside.

“Should I pull out?”

“No. Stay like that.”

I waited. I felt her body stop closing up. Then I pushed a little farther, millimeter by millimeter, until the ring gave way and my cock went deeper, caught by a tight heat that dragged a grunt from me.

“You’re opening me,” she murmured. “You’re really opening me.”

I didn’t answer. I couldn’t. I had to concentrate so I wouldn’t plunge in all at once. I added more lubricant, placed one hand on her hip, and began with short movements. I went in a little, pulled almost all the way out, and went in again. Clara moaned into the pillow, one hand between her legs, rubbing herself nonstop.

“Tell me if it hurts.”

“It hurts a little, but I like it. Don’t stop.”

That finally made me let go. I penetrated her deeper, until I felt my thighs against her buttocks. She gave a brief cry, went rigid for a second, and then began moving backward, seeking me.

“That’s it. That’s how.”

I fucked her ass slowly at first, heavily, letting every thrust go all the way in. Her anus squeezed my cock with delicious force, and every time I pulled almost to the tip, she shuddered as if afraid of losing me. Then she began pushing back against me again, more confidently, her voice dirtier.

“Put it all the way in again.”

I obeyed her. I grabbed her hips and began thrusting harder. The bed creaked. Clara touched her cunt desperately, her fingers soaked, her ass open for me, her breathing broken by moans and swear words.

“I never thought this would turn me on so much,” she said. “Never.”

I leaned over her back and spoke into her ear.

“Your ass was waiting for someone who wouldn’t be a brute.”

“Then fuck it properly.”

I lifted her onto her knees at the edge of the bed, still buried inside her. In front of the wardrobe mirror, Clara could see us: her bent forward, me behind her, my cock sliding in and out of her lubricated ass with a wet, obscene sound. The sight hit her full force.

“God,” she whispered. “I look like a slut.”

“You look beautiful.”

“No, tell me the other thing.”

I took hold of her hair gently enough to lift her face toward the reflection.

“You look like a slut who needed her ass fucked.”

Clara moaned so loudly that I had to clench my teeth to keep from coming right then. I sped up. My thrusts became harder, deeper. Her hands slipped across the mirror, her mouth hung open, and her other hand kept working her clitoris furiously.

“I’m going to come,” she warned.

“Do it.”

I held her by the waist and kept fucking her as the orgasm tore through her body. Her legs trembled, her ass closed around my cock with violent contractions, and she cried out my name with a shame she no longer tried to hide.

That squeeze dragged me over the edge. I gave three more deep, clumsy thrusts and came inside the condom, my forehead pressed against her back. I stayed still, breathing against her skin, still buried in her while we both came down at once.

When I slowly pulled out, Clara let herself fall onto the bed and gave an exhausted laugh. Her hair was stuck to her face, her cheeks were red, and she wore an expression of triumph I had never seen on her before.

“My body wasn’t the problem,” she said.

“No.”

“It was fear. And idiots.”

I lay down beside her. For a while we didn’t speak. Then she turned, kissed me unhurriedly, and rested her hand on my chest.

“We’re still friends, right?”

“Yes. Though now you know too much about me.”

“And you know too much about me.”

We laughed softly. We didn’t promise love or make absurd plans. That night didn’t fix her life or mine, but it gave her back something that had been taken from her: the feeling that her desire could have the final say too. And it left me with a confession I could never forget: sometimes friendship changes shape, gets naked, gets dirty, moans, and is still friendship.