The Hotel Date Was Hiding a Secret Under Her Skirt

Don’t call me a gigolo, even though I make a living seducing women for money. So what am I then? A whore? It’s not even their money I collect, and this isn’t my only source of income. I take it as a good deed, a kind of social work, a pleasurable pastime. The rumor passes from mouth to mouth, and that’s how I make new “friends.”

It all started as a joke. A guy I can’t call a friend, more of an asshole, blurted out that his sister was so plain there wasn’t a man alive who’d sleep with her, no matter how drunk he was. I took the challenge. I suppose I was pretty drunk that day too.

In the end the girl wasn’t that ugly or anything like that, and she turned out to be a much better person than her brother. We both had a good time. She was the first, and from there more opportunities came up. It’s just a supplement to my regular salary, nothing more.

The clients are husbands, friends, girlfriends, even fathers or brothers. Someone who wants to make them feel good, give them a good time. Sometimes they give me details about the victim, sorry, the target. Other times just a description or the number of a hotel room.

Usually they’re neither young nor pretty, and that doesn’t matter. It’s not as if I’m an Adonis either. I don’t have a bad body or a bad face, but I’ve got a certain charm, a way with words, or whatever you want to call it.

That’s why I was surprised when I walked into that fancy suite and found such a shy young woman waiting there. She must have been eighteen or nineteen, wrapped in clothes that were anything but provocative.

She wore a long skirt of light fabric, below the knees. Her blouse covered her entire torso, barely revealing part of her thin, white, soft arms. Her black hair fell below her shoulders. She had a pretty face, adorned with discreet makeup, and brown eyes so deep you could get lost in them.

She seemed nervous when she opened the door for me. I’d been told her name was Vanesa. She played with the end of a lock of hair, twisting it around her fingers.

Of course, I didn’t pounce on her. I’m no predator. I introduced myself and tried to make her laugh with a couple of dumb jokes. Her voice was barely a whisper, sweet and soft.

—Hi, I’m Darío. Your sister set us up here.

—I’m Vanesa. Yes, she told me you’re sweet and affectionate, that I can let myself go with you.

—I hope you trust me soon.

I managed to steal the first kiss from her, just the lightest brush of lips. She kissed me back shyly, but a little firmer, her hands in mine. They were soft; I liked stroking them, with those perfect nails painted bright red.

—You’re very pretty —I told her—. That shouldn’t stop you from having sex. Are you shy?

—Something like that. Yes.

Slowly I increased the intensity of my kisses, wanting more. Her lips, her tongue surrendering at the first touch. I realized she was taking it with more and more hunger.

She only pulled her mouth away from mine to tell me, in a voice rough with excitement, to be gentle with her, that she was a virgin.

—I’ve never been with anyone. Please be careful.

—Of course. We’ll go at your pace. Just relax and let yourself be carried by your desires.

I smiled at her and took one of her hands to my chest so she could caress me, so she could loosen up and start getting to know a man’s body. I didn’t even touch hers until she took off my shirt. I let her fingers follow the lines of my pecs, let her gain confidence. They brushed my nipples almost respectfully.

—You’re really hot. You’ve worked these muscles.

—I take care of myself. Now it’s your turn. I’d like to see more of that body you hide so much.

I stood her up and opened her dress all the way, letting it fall to the floor. The lace lingerie revealed her white skin, small breasts barely suggested, a waist so slim her ribs showed. She hung on my neck to kiss me again almost desperately, and at last I could grab her tight ass and pull her against me. The softness of her skin was driving me crazy.

Another wave of shyness hit her and she only said:

—Forgive me.

—For what? You haven’t done anything wrong.

Then she took my hand and led it to her pubis. From between her thighs a cock had begun to emerge that, while not big, wasn’t small either. Thin, straight, neatly shaved. And it seemed our kisses were making it hard. I had to move the lace aside so it wouldn’t hurt her.

I should have been blind not to realize it before, but her shyness had thrown me off. I didn’t like the trick I’d fallen for. But the sweetness of that girl made me kiss her again, sucking on her tongue.

—It’s all right. To me you’re a real woman. And we’re going to prove it. No rush.

I promised her I wouldn’t leave without making her a woman. I wanted to rip off her lace panties and matching bra to enjoy her beautiful androgynous body.

—Are you on hormones?

—For a little while now, yes.

—It suits you. Very well, from what I can see. You’re going to be a beautiful woman.

I think she even blushed. But she was getting aroused in leaps and bounds and wanted more. With my caresses, her cock had gotten rock hard. I was getting horny too, having that pretty rod in my hands. I kept stripping her. With one hand I unclasped the bra and left it hanging from my fingers.

At last I could admire her small, firm breasts. The proud, dark-red nipple crowning two barely pointed cones of flesh. From her sweet lips I moved to her ear, to her neck, to her shoulder, to those little tits calling to me. I never let go of her hip, but I still didn’t want to free her from the thong. I just kept licking her skin.

I traced her armpits, the marked ribs, the flat belly, the navel. My tongue moistening her soft skin, her moans flattering my ears. When I reached her pubis, it was time to pull the thong down her long thighs. It snagged for a few seconds on the stiffness of her cock, but I managed to get it off over her carefully tended feet without further incident.

Taking advantage of having her hands there, I brought her fingers to my mouth and started sucking on them. I wanted her to understand that no part of her body disgusted me before I brought her shaft to my lips. That every one of them could give her pleasure.

I went up licking her calf, the inner side of her thighs, until, smiling and looking into her brown eyes, I ran my tongue over her shaved balls. I devoted myself to sucking them for a while. From there I slid my tongue along the shaft, thin and straight, with visible veins, up to the glans, as purple as the inside of a pomegranate and hard as a stone.

—Stop! You’re going to make me come.

—Better. Let yourself go.

I gladly took her seed in my mouth. It wasn’t the first I’d tasted, and when I like the person I do it happily. But with her it was special. I savored that flavor for a second before sitting up and offering it back to her in a lustful kiss. She opened her mouth and eagerly accepted my tongue, my saliva, and her own semen.

I grabbed her rock-hard ass, pressing her body against mine. She was trembling with anticipation. I kissed her neck, her ear.

—Want to taste mine?

—I’m dying to. It’s my first cock, you know?

—I figured as much. Do whatever you want, and whatever I want too, as much as you do.

I lay down beside her on the mattress. She was still breathing hard. I opened my legs so she could settle between my thighs, on her knees. Seeing her little face turned toward me, half-hidden by strands of hair, looking me in the eyes, was incredibly arousing. She had tucked her flaccid cock between her legs; it must have been her habit. She did it without thinking.

For a while she stared at my dick with an amazingly horny look on her face. She moved it from side to side with her hand to see it all, lifting my balls. Her curiosity was making me feel weak at the knees.

At last she decided to run her tongue over my skin. A shiver ran through my body. From there everything flowed naturally: she started sucking my balls, moving up the shaft until she reached the glans. She tried to take it in her mouth, but gagged.

—Easy, darling. You don’t need to do that. Just lick it. Suck the glans and the balls like candy. Think about what you like. Anyway, you’re going to make me come. You could make any man happy with those lips.

I said it softly, gently, stroking her hair and shoulders with tenderness.

—But I want more. I want everything.

—Don’t be greedy, we’re in no hurry, I already promised you that. Would you want to fuck me?

She interspersed her broken phrases with licks to my cock and moans. From time to time she took a hand to her sex and stroked herself. She was getting hard again.

—Would you let me?

—Anything you want, darling.

—And you, are you going to penetrate me? I want you to make me a woman, but I’m afraid it’ll hurt.

—That’s what the lube is for. We’re going to do it together. Just enjoy yourself.

With her tongue running over my genitals and that conversation, I was more than aroused.

—I’m going to come, darling. Where do you want my semen?

—I’m not going to waste it. On my tongue.

And that’s how it went. She kept sucking until I spilled into her mouth. She didn’t stop there: she leaned up to kiss me and shared my cum in a new kiss. We crossed tongues for a good while, never stopping our gentle caresses.

We both wanted more. She was looking for my cock, which with her kisses was hardening again. I was stroking her ass, sliding a finger over her asshole and starting to stretch it, slowly, tenderly. I reached for the lube and started applying it, first with one finger, then two, opening her tight little hole. She moaned.

—Ride me yourself. That way you’ll have more control.

She spread more lube over my cock with her little hand, making it even harder. I lay on my back, my dick pointing at the ceiling. Her hips looked tiny between my hands as I lifted her on top of me. With her knees on either side of my body, she slowly lowered her ass. My cock went in slowly, firmly. At no point did she pull back.

The moans coming from her lips told me it didn’t hurt, that she was enjoying her first time.

—Mmm. So good.

—Slowly. Feel it.

I took the opportunity to stroke her hard cock, pointing toward my face, and to pinch her nipples gently. But I didn’t want her to come yet; I was saving her for my ass. She, on the other hand, was looking for my semen in her rectum. She didn’t stop moving up and down, slow but firm, until I had my orgasm.

She collapsed onto my chest, exhausted, kissing my neck, my lips, even my nipples. I stroked her hair, her back, her hard little butt.

Her stiff cock was trapped between our bellies, throbbing, eager to unload. And I wanted it to do it inside me. So I lifted her and offered myself to her. I wanted to see her face while she fucked me. I lay on my back, opened my legs wide, and lifted them to my chest.

—Your turn. Stretch me and lube me up.

She drove two fingers, well coated in lube, into my ass. I could feel her digging inside me, and I loved the sensation. I was enjoying it.

—Come on, put it on your cock and shove it in me.

With a wicked little smile she began to coat her shaft with lube. Her nipples looked as if they wanted to escape her chest.

—Ready?

—Desperate. Go on.

She set the glans against my hole and pushed slowly. It wasn’t my first time, but I wasn’t exactly used to having a dick in my ass either. It helped that hers was so thin and that she took it slow. It hardly hurt at all, and I started moaning and panting the way she had a little earlier. She leaned down and stroked my nipples while she fucked me.

I realized she was loosening up at a dizzying pace. She was going to make her next lovers very happy with her kink. I received her semen in my ass, and she did something I would never have imagined when I saw her walk into the room. She bent down and started licking my anus, collecting the semen that came out when I tightened my stomach muscles. I almost came again at that moment, even though I didn’t even have my cock fully hard.

I pulled her into my arms to rest and recover.

—You’re learning, all right. More than I taught you.

—That’s because you’re a terrific teacher.

She smiled at me as she hugged me tightly, and I held her.

—Are you happy?

—It was amazing. I’m enjoying it a lot. I think I’m starting to gain confidence.

—You should dress sexier. These rags don’t do you justice. You’ve got very nice legs, show them off.

—Until now I didn’t dare. I wanted to be invisible. But little by little I’ll have the confidence to show more.

I kept drawing confessions out of her while we caressed each other. Doing a little psychological counseling is part of the job. Of course, it’s easier to do it naked, pressed close together on a bed, than on a therapist’s couch. She told me that her sister, the one who had brought us together in that room, was the one who supported her most, and that her determination was firm.

***

Since then she’s kept improving, and now she’s a beautiful woman with a thin, straight cock that gives me pleasure from time to time, just as mine pleases her, with no money involved anymore. We burned the rags she used to hide her body behind. She dresses much sexier now. We fuck because we feel like it and because we like it. And sometimes, when she looks at me with that horny little face, I think the best job of my life was never a job at all.