Her First Night as an Escort Was with Me

We got to the club almost without speaking, because the music was thundering from the entrance and going in felt like plunging headfirst into a wave of bass. We spent an hour and a half inside, and out of that whole hour and a half I’m left with four songs: the ones we danced to together, where Daniela made it clear that her Cuban blood was no decorative detail. She danced salsa pressed against me, glancing at me out of the corner of her eye, but it was the bachata that really left me dazed. She moved her hips as if she wanted to draw something on my thigh, and when she turned she offered me her ass, barely brushed by her short dress.

Talking inside was impossible. I took advantage of the fact that she was driving that night and ordered three whiskeys on the rocks. Daniela kissed me on the mouth from time to time, slowly, to taste the trace of whiskey on my tongue. She’s beautiful from head to toe, not just from the back, though I had already noticed the effect she had: while I waited for her to come back from the bathroom, a man of about forty came over, leaned in respectfully, and whispered in my ear, “your company is spectacular, man, what a beautiful woman.” I smiled, thanked him, and went back to waiting.

We left after midnight, our whole bodies already asking for what the dance floor had promised us. Daniela was driving with a restrained smile; I watched her profile and thought about the toys we had bought that very afternoon, still sealed in their boxes. She was twenty-two, and that was her first night as an escort. She had said it like a confession, not a lure, and that was why I believed her.

We wasted no time in the hotel room. We got into the shower together and let the hot water cover us while I stood behind her and kissed the back of her neck. My cock settled between her buttocks, and the head slid up and down as it pleased, sending a visible shiver through her skin. I spoke to her ear with the tip of my tongue circling her lobe.

—Do you like feeling it there? —I asked.

—Andrés, I love it. It tickles me all the way up to my neck.

—And lower down, near the entrance?

—Even more. Even more.

—Had you ever felt a cock between your ass cheeks?

—Never. Hold me, touch my tits. Don’t stop.

We stayed like that for a long while, the two of us still under the water. I slipped my hand between her legs and confirmed she no longer needed any more warming up: she was soaked with something that wasn’t water. This time I was the one who dried her, unhurried, kissing her shoulders and the nape of her neck, discovering every centimeter of that body she was paying to have but that never once felt bought. I carried her to the bed and put her on all fours. The very position she had confessed a little while earlier embarrassed her to take.

She didn’t say anything. She let me do it, and I massaged her buttocks with both hands for several minutes, touching nothing else, until she herself began to open her legs a little. I knelt on the mattress, tipped her torso down until her breasts were pressed to the sheet, and her ass appeared in that impossible curve that seems drawn to drive someone insane.

I put one hand on each cheek and kissed the lips of her shaved vulva. Just that. She moaned softly and pushed her pelvis forward, looking for more. I ran my tongue slowly, from bottom to top, and let myself sink just barely into that sweet, hot groove. She smelled of hotel soap and young skin. I stayed there for about five or six minutes, until her moans began to drift into another dimension, and then I decided to move up.

I ran my tongue over the perineum, unhurried. I made her think I was going somewhere and took her somewhere else. Millimeter by millimeter, I worked my way up to the edge of that small tight ring that clenched every time my breath brushed it. Her vulva began to release a thick, almost dense fluid that ran down her thigh. She could guess what was coming and burned inside with that anticipation.

—My God —she said, her voice trembling when I finally pressed my whole tongue against her asshole.

Maybe it was similar to the first time in her life she came, still a kid, rubbing against the ridge of a pillow without understanding what was happening to her body. That afternoon now was something else: it was discovering, almost at twenty-two, that a kiss on the ass can be as natural as a kiss on the mouth. And that same tongue that had been looking for me hours earlier could stay there, moving up and down, until it drove her crazy.

I hadn’t expected her to react so quickly. She started moving on her own, driving her hips against my face as if she were being rammed, and her sphincter throbbed against my tongue with a strange urgency, as if it didn’t quite know what to do with it. She told me so between gasps.

—Andrés, I’m coming. You’re making me come. So good, my God. I’m cumming.

She let herself fall face-down on the bed and I held her by the hips to push into her cunt in one thrust. She was crying out, not holding back, and another orgasm hit her before I even did anything. I pumped slowly for two or three minutes, until her breathing evened out a little. She turned her face toward me, smiling halfway, still not quite believing what had just happened to her.

—You’re going to kill me. What was that?

—Did it feel good when you came?

—Good? That was an attack. I was not expecting that at all.

—I loved your cum.

—This can’t just be called sex. It should have another name.

—You liked it that much?

—Look at my hands. My thighs are shaking. —And she laughed without really laughing.

—Must have been a multiple orgasm.

—I don’t know what that was. I just know I had never, ever come like that.

—But did you like feeling my tongue on your ass?

—You already know the answer. But I didn’t expect to end up like this.

—Do you want more?

—Let me breathe. And you?

—We have all night.

While Daniela recovered on her back, I got out of bed, took the three toys out of their boxes and put batteries in them. I rinsed them with soap and laid them out neatly on the nightstand, from smallest to largest. Then I suggested a position that with almost every woman I’ve known eventually becomes a favorite at some point in the night. It’s a reverse of woman-on-top: she lies face-down, on her breasts, opens her legs and lets me enter from behind, with her ass perfectly exposed for me to do whatever I want with it.

—I love this ass —I told her, massaging it slowly—. I can’t stand the urge to be inside.

—Apparently you know what you’re doing. Just look at you, making me come like that.

—On a scale from one to ten, how much did you like it?

—A thousand. A thousand, Andrés. I still don’t understand what you did to me.

—Don’t try to understand it. Just enjoy it.

—This is good too. Feeling it inside and having my ass massaged. I’m in heaven.

—Let’s try something new. If anything makes you uncomfortable, tell me and I’ll stop.

—Deal. But so far I’ve loved everything.

—I’m going to try to get in here —and I rested my thumb on the ring of her asshole—, but I want you relaxed. If you tense up, it hurts.

I coated my thumb with lubricant and stroked her asshole in circles. I pressed just slightly, without forcing it, while keeping my hips moving inside her vagina. I could feel every contraction in my cock: she had incredibly tight walls, and that was confirmed every time she clenched around me. When I managed to sink in the first knuckle of my thumb, a warm liquid ran down the inside of her thigh to my balls. She squirmed and whispered.

—Andrés, that feels so good.

I took the first dildo, the smallest, no bigger than a pinky finger. The girl at the store where we’d bought them had called it “the boyfriend you don’t notice.” I smeared it with anal lube, set it to medium speed, and placed it at her entrance. Daniela let out a long moan, and little by little the four inches disappeared inside her.

—Do you like it?

—It feels so good. I think I’m going to come again.

We stayed like that for a couple of minutes, her rocking against my balls each time the toy sank in. When I saw she had gotten past that first strange sensation of having something unfamiliar inside her, I decided to move up a level. The second dildo was nine inches, with a serious thickness and a curve at the tip that demanded going in slowly. I reminded her to relax her muscles, to think about opening rather than closing. I spread lubricant all over her asshole and began the maneuver.

She tensed at first; I noticed it in her shoulders. I spoke softly to her, told her how gorgeous her ass looked from where I was, what it made me feel to have her like that. I told her I loved her lips, her tits, her legs, everything. And while I talked, the dildo sank all the way in. I felt the vibration through the inner wall of her vagina, against my own cock. Daniela couldn’t take it.

—Andrés, I’m going. I’m going. My God, you’re going to finish me off. So good.

Her sphincter was already stretched and you could tell. I arranged her on her back, with her legs open toward me, and grabbed the last toy: the inflatable, coated with menthol lubricant. I leveled her asshole with my cock, and without me saying anything she offered me her ass to make access easier. I pushed my cock into her ass, slowly, while I set the dildo in her cunt on the first vibration level. It was she who moved, who set the rhythm of the rocking, sliding my cock in and out as if she’d been doing it for years.

I inflated the dildo just a little and moved up to the second speed. The sensation multiplied for her: her pussy was full of a vibrating toy and her ass invaded by me. The only thing I could do was watch her face. She moved her hips as best she could, until a huge orgasm shook her whole body, and this time tears spilled out of her, not from pain but from somewhere much deeper. It was so much that I couldn’t hold out: I came inside her almost without moving.

—You’re going to kill me.

—I felt so good cumming in your ass.

—I had never come like this before. This is the best fucking of my life.

—You’re only twenty-two.

—You really know how to fuck. I don’t know how many orgasms you’ve given me. I lost count.

—Your ass inspired me. You’re beautiful, Daniela.

—I like you a lot too. I can’t believe you’re forty-seven. Not at all.

—I want to fuck your ass again, on all fours.

—What can I say? It’s yours.

—Did it bother you?

—A little burning, that’s all. You can fuck me again if you want.

***

I fucked her ass on all fours, then face-to-face sitting on top of me, then from behind. I also had her ride me missionary because she asked me to suck her tits. I came five times in total: once in a slow blowjob, once inside her cunt, and three times in her ass. When the alarm went off at nine in the morning, I didn’t know whether I had slept or not. We showered together, without so much fuss this time, and she put on black sweatpants with a yellow thong and a red blouse. She looked even younger than the night before.

In the car, on the way to her building, we talked nonstop.

—I admire your stamina. I never imagined the marathon waiting for me.

—Did I really make that impression on you?

—Impression? Andrés, with that doll’s face of yours, any woman would give herself to you.

—I’d like to see you again.

—We have to see each other again. I want to feel, even if only one more time, what we did last night.

—Did you like the anal?

—Did I like it? I loved it. Andrés, you’ve got me hooked on anal.

—Can I ask you something?

—Ask me.

—Will you give me the thong you’re wearing?

—This one and any other you ask me for.

—Then give me all of them. I want to take them as a keepsake.

We got to the parking lot of her building, and with a very her move, sensual but practical, she took off her thong inside the car, looked for the others in her suitcase, and left them in the glove compartment. She kissed me long and hard on the mouth. When she pulled away, I laughed. She looked at me, puzzled.

—What are you laughing at?

—You know, I always thought the whole thing about it being your first night as an escort was a lie.

—It’s the truth.

—I know.

—How do you know?

—Because we’re saying goodbye and you’re forgetting something.

—Sorry. Let me give you another kiss. —I kept laughing, and she got uncomfortable—. I don’t understand. You’re making fun of me.

—I’m not making fun of you. It’s just that the agency asked me to pay you fifteen hundred in cash. The four hundred they charged to the card, I assume, are their commission. You didn’t ask me for your share, and I had such a good time with you that I can’t leave without giving it to you. —And I handed her an envelope with the money.

—And what if we forget about this?

—What do you mean?

—Forget it. I want you to forget I’m an escort. I want to be just a friend with some rights. I don’t want you to remember me as an expensive whore. I want you to remember me as a girl who had something huge happen to her with you.

—Is that what you want?

—Yes, that’s what I want.

—You’re going to keep working for the agency.

—I don’t think so. I fulfilled my fantasy. I wanted to fuck someone I didn’t know. That’s what I was looking for.

—What are you doing this weekend?

—Nothing.

—Do you want to pack your bag again and go to Cancún with me for five days?

—Really?

—I’ll pick you up at four in the afternoon.

—I’ll be waiting.

—What name should I put the ticket under? Because I doubt your real name is Daniela Vargas.

—My name is Mariana.

—Nice to meet you, Mariana. Do you want to be my girlfriend?

—Give me some time. Four hours to give you an answer worthy of the question.

—Don’t feel pressured. I just want to break your little ass open again.

—Andrés, it’s yours. Come get it this afternoon.

I booked the flights that same afternoon and we went away for the full five days to the coast, to a hotel facing the sea. We fucked nonstop and since then we’ve kept seeing each other, with no name for what we have. Mariana, or Daniela when her old girlfriends call her, always repeats the same thing to me: Andrés, my ass is all yours.