How I Taught My Friend to Charge for Pleasure

Only four days had passed since our night with Javier and Luciana, the encounter that marked the two of them’s bisexual debut, and they were already calling me separately to say the same thing: that it had been incredible, that they wanted to do it again, that they couldn’t stop thinking about it.

Javier, in particular, had a clear goal for next time. He wanted Luciana to be able to enjoy anal sex without suffering or tension. They’d been trying for months, but his size turned every attempt into more effort than pleasure. He asked for my help bluntly. He trusted me, and I agreed.

They lived in Mar del Plata, more than a hundred kilometers from Buenos Aires. I already had my weekend booked with my own clients —two mornings and two afternoons reserved weeks in advance— so I invited them over on a Thursday night. First we’d have dinner out, and then what everyone was imagining.

I chose a restaurant I know well: warm, discreet lighting, tables spaced apart, a decent wine list. We arrived at eight, asked for a table in the back, and settled in with time to spare.

The conversation flowed easily. I told them something few people knew: that I was planning to leave the consulting firm where I worked to set up my own practice, focused on foreign companies that needed strategic reports. I already had my eye on an apartment with the perfect ground floor for seeing clients from both sides of the business. My double life, orderly and discreet, under one roof.

As we talked, I noticed that at a nearby table two men alone —loosely tied neckties, a conversation that looked like work— were watching us with that kind of discretion that isn’t really discretion. We were four people, two women dressed suggestively but not over the top, and they couldn’t help themselves.

I whispered to Luciana:

—Do you see them? A place like this, well chosen, on a Thursday night, is exactly the kind of setting where you can find the kind of man worth it. Professional, probably married, discreet out of necessity.

—The idea is becoming more and more tempting —she replied, turning her glass between her fingers.

—If you want, at the end of dinner Diego and I will leave first. I’ll kiss you on the mouth when I get up, so there’s no doubt about the dynamic between us. Javier can pretend he’s going to the bathroom for a few minutes and leave you alone. Discreetly, no rush. If either of them comes over, you know what to say.

I handed her two contact cards —just the phone number, no name or company— so she’d have them handy when the time came.

We kept eating without rushing. I explained what to do if either of the two approached: be friendly, hint that she wanted to spice up her marriage, that maybe she’d consider an offer that really motivated her. Nothing explicit. If they called later, I’d mediate at first.

—What matters —I told her— is that you don’t have to say anything hard. Just let them carry the conversation. A smile, a few ambiguous words, and the card on the table when you leave. That’s all.

—And if they ask me how much?

—You talk about that by phone, never in person the first time. You tell them to call you.

When dinner was over, we left our share of the money on the table. Diego and I stood up and said goodbye. I kissed her briefly on the mouth, unbuttoned one more button on her blouse as if it were nothing, and smiled at her. Javier came out a few minutes later, claiming he was going to the bathroom.

We waited on the sidewalk. I lit a cigarette and didn’t finish it.

***

We were halfway home when my phone rang. Unknown number. I answered.

The man introduced himself as Marcos. He said he’d seen us having dinner that night and asked if I was “the lady who was left alone at the end.”

—No —I replied—. That’s a friend of mine. You’ll find her at my place in a little while. And if she let the card slip, it was probably by accident.

—I liked her a lot —he said—. Could I call her?

—You can call this same number in an hour. She’ll be there.

—Is she married?

—Yes. Married and maybe looking for something special.

—Married and discreet is exactly what I’m looking for.

I hung up. Diego didn’t say anything, but he smiled.

When we got home, Javier and Luciana arrived minutes later. I brought them up to speed about the call. Javier laughed hard. Luciana fell silent for a second and then asked whether they were really going to call.

—They already called —I said.

I suggested she take the initiative herself: call, negotiate, set something up for the next day before they went back to Mar del Plata. Better now, with the mood already hot, than tomorrow with fear on top of her. They both nodded.

I called first from my phone, as a precaution. Marcos answered. I passed the phone to Luciana.

What followed was a long, careful negotiation. Luciana was genuinely shy, and Marcos had the caution of a man who didn’t want to get into trouble. Meanwhile, Diego and Javier slowly undressed me on the living room sofa, unhurried, letting her talk.

Diego pulled my dress over my head and left me in my underwear, kneeling between the two of them. Javier groped my tits over my bra, squeezing them with both hands, pinching my nipples until they stiffened against the fabric. Diego pulled my panties down to my knees and slid two fingers into my cunt at once, without preamble, searching for the right spot with his fingertips. I was already wet. He chuckled softly when he noticed how soaked his fingers were, and ran them over my lips for me to suck them clean. I licked them while Javier took off my bra and sucked one whole breast, biting my nipple just enough for a moan to slip out of me, which I had to swallow so I wouldn’t ruin Luciana’s call.

Luciana explained that we were two very close couples, that I was “the boldest one,” that I even accepted gifts from gentlemen. The inevitable question came.

—And would you accept something like that?

Luciana hesitated. She looked at me. I had Javier’s cock in my mouth at that moment, going in and out slowly, and even so I managed to nod without letting go. She understood.

—I’ve been thinking about it for a while —she said—. It’s hard for me to take the step. Although my husband supports me if I really like the idea. And the truth is... I do like it.

They agreed on a price. Important. Lower than mine, which was expected for a first time, but still very decent. Marcos insisted on some proof that what they’d discussed was real.

Luciana held out the phone to me without saying anything. I understood what she was asking for.

I told Marcos to wait ten minutes. If he was alone or in good company, we’d call back. He ended the call.

The men stopped touching me and undressed Luciana with the same calm they’d used with me. They took off her blouse, her skirt, left her in a black thong in front of the two of them. Javier spread her legs right there on the sofa and ate her cunt with his mouth open, sucking her clit until she arched her back and grabbed his head with both hands. Diego positioned himself behind her, against her back, his hard cock pressed against Luciana’s ass like a warning of what was coming.

I dialed again, this time by video call. When Marcos answered, Luciana was already riding Diego, impaled to the hilt, moving her hips in slow circles with her head thrown back. I filmed from behind, without focusing on faces: the arch of her back, Diego’s cock sliding in and out between her ass cheeks, her tits bouncing when she turned her head. Ten seconds. I cut the call.

I called by voice a minute later. Luciana closed the details with a broken voice, still sitting on top of Diego, moving just enough not to moan into the phone: tomorrow at ten, in a hotel she would choose near Retiro station. Marcos would confirm the room number by message.

***

That night was long and good.

The four of us moved into the bedroom, naked now, skin hot and mouths dry with wanting. Luciana climbed on top of Diego while Javier impaled me from behind, on all fours, leaning over her so we could kiss. It was a position that demanded concentration, but we found the rhythm. Javier drove into me to the hilt, gripping my waist, and started fucking me with those sharp, deep thrusts I knew from the previous time. I could feel every centimeter of his cock going in and out while Luciana’s tongue tangled with mine. Each push from Javier pulled me forward and made my lips crash against hers, and she laughed into my mouth and sucked my tongue.

Diego held her by the hips and lifted her up and down on his cock, setting the pace. Luciana started moaning loudly, her mouth against my neck, and I felt her cunt tighten because Diego brought his hand down and found her clit with his thumb. She came like that, trembling, with Diego’s cock inside her and my breast in her mouth. A minute later Diego finished inside her with a long groan, sinking all the way in. Javier held out a little longer, kept fucking me faster and faster, until he dug his fingers into my hips and came inside me in three long spurts that I felt hot against the wall of my cunt. He stayed there a moment, leaning on my back, breathing hard, before slowly pulling out and leaving me soaked, semen running down my thighs.

The men left us alone for a while to recover.

There’s something very different for me with a woman. Not better or worse, just different. Slower, more attentive. Luciana lay me on my back and opened my legs with both hands. She bent down and licked my cunt, full of Javier’s cum, without disgust, with her tongue flat and long, going from the opening to the clit. No one had ever done that to me like that, with that calm. She sucked my clit between her lips and slipped two fingers inside me at the same time, curving them, searching for that spot most people never find. She found it. I grabbed her hair with both hands and pressed her face against me, coming in her mouth with a cry that escaped me without my even realizing it.

Then I returned the favor. I put her on some pillows, with her legs spread wide, and ate her cunt with my mouth full of saliva and Diego’s taste still on my tongue. I sucked her clit, nibbled it gently, shoved my tongue inside as deep as I could. She pulled my hair, writhed, said my name. We took our time. We laughed once, for no reason at all, and that was part of it too.

When the men had rested, they came back to the bedroom with another purpose. That was what we had planned from the start: preparing her for what Javier had been wanting to achieve for months without success.

The two of them worked on Luciana together. First tongue in the ass, a long time, taking turns between them, with Diego’s pointed tongue slipping in and out of her sphincter while Javier sucked her cunt from above. Then fingers: one first, then two, with plenty of lubricant, until the muscles in her body truly relaxed and she began pushing against Diego’s hand, asking for more.

Diego penetrated her first anally —his size was manageable, comfortable— and Luciana took him well, with controlled breathing and loose shoulders. He advanced without rushing, centimeter by centimeter, until he was all the way inside. He started fucking her slowly, with long strokes, and she moaned softly, surprised to be enjoying it. After a long while he came inside her, leaving her ass lubricated from the inside with his cum.

But that wasn’t enough to prepare her for Javier. Something more was needed.

I left the bedroom without saying anything.

When I came back, I was carrying something none of the three expected to see. It was a long, thick black silicone dildo, with no harness required. It held itself in place with two internal protrusions that fit into the body and kept the whole apparatus completely firm. I’d bought it at a specialty shop in Berlin the year before and hadn’t had the right occasion to try it out.

I slipped it into myself right there, in front of them: the short end went into my cunt and ass with a firm push, and once it was in place it felt like it was part of me. I stood in front of the large wardrobe mirror. I looked at myself: blonde, breasts bare, that dark erection sticking out of me, hard, obscene, as big as Javier’s or bigger. The image was completely unexpected and, I have to admit, I loved it. I moved my hips and the cock moved with me. I grabbed it with my hand and pumped it a couple of times, like a man would. The three of them watched me in silence.

Luciana looked at me with wide eyes from the bed.

—Are you going to do that to me? —she asked.

—I’m going to prepare you so you can really enjoy your husband —I replied—. You both deserve it.

I carefully applied anesthetic gel to her sphincter, waited for it to take effect, and coated the dildo with lubricant until it shone. I put her on all fours, with her head on the pillow and her ass raised. I spread her buttocks with both hands and rubbed the tip over her hole slowly, in circles, until she started pushing back, looking for me. I guided the tip with my hand. I pushed very slowly. The head of the dildo went in and she took a deep breath, focused. There was no tension in her body this time. I kept pushing, centimeter by centimeter, watching the black silicone disappear inside her.

When I saw her smile faintly against the pillow, I pushed all the way in, until my hips hit her ass.

—Yes —she said—. Yes, more.

There was no more. It was all the way in.

I started fucking her. At first slowly, pulling almost all the way out and sliding it back in calmly, watching the sphincter stretch around the black dildo. Then faster, gripping her hips the way I had seen men do so many times. Luciana moaned louder and louder, pushing her ass back against me, asking for more. Javier and Diego watched from the side, their cocks hard again, saying nothing. I fucked her like that for a long while, until she came with the dildo inside her ass and Javier’s fingers in her cunt, trembling and shouting.

I pulled it out slowly. Her sphincter stayed open, won over, ready.

Javier didn’t wait: he climbed onto the bed, grabbed her by the hips, and entered her in one go, all the way. There was no scream, no resistance. Only a long, surprised moan, genuinely satisfied to finally feel her husband all the way inside her without pain.

He fucked her hard, slowly at first and then with all the conviction of a man who can finally do it. He grabbed her hair and pulled, bit the back of her neck, drove his cock to the hilt over and over, listening to the wet slap of his hips against her ass cheeks. Luciana pushed back with her hands on the headboard, moaning with every thrust, asking for it harder, deeper. When Javier came, he sank all the way in and stayed there, growling, emptying himself inside her with his forehead pressed to her back. Luciana was sobbing and laughing at the same time, face buried in the pillow, with her husband’s cum dripping inside her ass for the first time.

The four of us hugged. Quick shower. An hour more in bed, calmer, some wine, and sleep won over all of us.

***

Javier went back to Mar del Plata at dawn. Luciana would stay until after her appointment with Marcos.

We slept little. By eight we were already having breakfast in the kitchen, and in that time I gave her everything I could think of.

I told her to ask for the money before starting, without apologies or detours. That if something made her uncomfortable, she had every right to get up and leave, and that no worthwhile man would object to that. That she should use a condom always, no matter what he said or proposed. That she should choose a room with a lock she could manage herself.

—Are you nervous? —I asked her.

—Very —she admitted.

—Good. That means you’re taking it seriously.

We also talked about what was coming. When I had the apartment ready, she’d be welcome whenever she wanted. No obligation, only if she felt like it. Besides, an acquaintance of mine —the owner of a ranch in the province— had long ago proposed a meeting that fit perfectly with the fantasy Luciana had once told me in a low voice between the sheets.

—The open-field thing? —she asked, a little flushed.

—That one. When you’re ready.

—At this rate I’m going to be ready for everything sooner than I imagine —she said, and laughed at herself.

At nine I drove her to Retiro station. Marcos was waiting on the opposite corner: dark suit, hands in his pockets, a look that swept the sidewalk twice before finding her. When they saw each other, he smiled first. That was a good sign.

I watched her walk away beside him. I started the engine and went back home.

***

Three hours later the message came in.

“On the bus back. With the envelope in my bag and still shaking a little. Marcos behaved very well, paid without drama, and was satisfied. Thank you for everything. You’re my idol.”

I asked her how she felt.

“Happy. Fulfilled. Scared by how well it went.”

I replied that the best was yet to come, and it was true. I had agreed with Marcos that next time it would be without a condom, once they exchanged test results. Following my advice to the letter. It was exactly what I would have done.

I put the phone away and turned on the computer. I had a strategic report to finish before afternoon. Another client, another life, the same desk.

I smiled to myself in the empty kitchen and thought that, in the end, teaching has its rewards too.